Sissyboy Stories

140 results
Orientation
Length
Source
Infinite Scroll

Sandra and Stevie Ch. 63

by Goodhusband on Sep 19, 2017
Loving Wives

Note: This story is the sixty-third installment in a series entitled "Sandra and Stevie". If you have not read the previous sixty-two episodes of this series, I encourage you do so before beginning this chapter. This is a dominant wife humiliates submissive husband story. That is the kind of story I write. If you do not enjoy these types of stories, I stron...

Secrets of The New World Order Ch. 06

by bjmichaels on Sep 16, 2017
Sci-Fi & Fantasy

Your child's eighteenth birthday marks a significant rite of passage every mother faces with ambivalent feelings...soon, the child will be out of the house on their own, meeting new challenges every day, and all you can do now is hope you've prepared them for the highs and lows the real world will throw at them. In my case, it meant I had just one child rem...

Constrained in Corsetry

by susanxdresser on Sep 16, 2017
Transsexuals & Crossdressers

Although I am not into serious bondage I love the erotic pleasures of wearing corsetry and other tight feminine garments next to my skin. When wearing suspenders and stockings I love the erotic sensation from the tightness of the top of my stockings gripping my thighs and the suspenders brushing against my thighs as I walk, as I envisage my suspender belt an...

Mistress Kate Pt. 02

by corduroysissy on Mar 7, 2018
Transsexuals & Crossdressers

When he arrived home from Regan O'Reilly's office Jordan was still in a daze. He needed a drink, no scratch that, he needed a bottle. In a matter of a couple hours he'd gone from having his life threatened, to getting a blowjob from the Leprechaun, to being ordered into sissy sexual servitude by Mistress Kate. She was actually expecting him to be her fucking...

Casey's Submissive Journey Pt. 12

by corduroysissy on Jul 31, 2018
Transsexuals & Crossdressers

Mistress Maxi -- Part 1 Maxine Montgomery was sixty-four years old, five-foot seven-inches tall, and one hundred and forty pounds. She was an attractively handsome woman whose looks and demeanor were very similar to the character Katherine Chancellor on the soap opera The Young and the Restless. "Distinguished" was a very good adjective for Maxine, "arrogan...

Mistress Sharon Pt. 01

by corduroysissy on Sep 5, 2018
Transsexuals & Crossdressers

Dana had just finished moving his corduroy girly clothes from the washing machine to the dryer when the phone rang. Being a closet fag and having a corduroy fetish, he not only dressed often but jerked off with his wardrobe on a daily basis, sometimes two or three times a day. As you can imagine that created a lot of sperm stains, and his skirts and dresses...

Mistress Sylvia Pt. 02

by corduroysissy on Dec 19, 2018
Transgender & Crossdressers

Having gotten a good look at what would be his future living quarters, Debbie followed Mistress Sylvia through a doorway and down a second corridor of bedrooms. She explained that the rooms were where the fags did their whoring, and the door at the far end of the hallway was the client's entrance. Just before the end of the hall was a set of double doors on...

Casey's Submissive Journey Pt. 09

by corduroysissy on Jul 17, 2018
Transsexuals & Crossdressers

A day With Dorothy -- Part One - The Players Casey -- Submissive closet sissyfag with a corduroy fetish, owned by Karen. Karen -- Wife/Mistress to Casey and member of the Lady's Club. Julian - Submissive closet sissyfag owned by Dorothy (Dottie) Dottie -- Wife/Mistress to Julian and member of the Lady's Club. Maxie -- President and founder of the Lady...

Casey's Submissive Journey Pt. 13

by corduroysissy on Aug 1, 2018
Transsexuals & Crossdressers

Since Susan had been treating him so nicely, Debbie suddenly felt a little strange when she abruptly walked out. Seeing the confusion on his face, Maxi said. "Don't worry Debbie she has things to do, she'll be back when she's ready to cum again." She slowly smiled. "Oh my, how amusing. Did you think you two were girlfriends now?" She chuckled. "Sorry siss...

Jennifer Monroe & the Ladies Ch. 03

by corduroysissy on Jan 31, 2018
Transsexuals & Crossdressers

Debbie gave Miss Jennifer's boot one last kiss, took a few seconds to straighten out his dress, then walked over and knelt submissively next to Patty in front of Miss Marsha. She let Patricia continue to suck her dick and lit a cigarette, she didn't even look at him, in fact she totally ignored him for several minutes. She did however blow smoke in his face...